Proposal Writer + Project Manager

Company Description

DoodleWeb is a digital agency that specializes in transforming innovative ideas into impactful digital experiences for startups, eCommerce brands, and growing businesses. Our expertise spans UI/UX design, web development, eCommerce solutions, and digital branding to deliver intuitive, scalable, and results-driven solutions. With a proven track record across various industries, we offer end-to-end services from concept to execution, leveraging user-centric design, technology, and data. At DoodleWeb, our mission is to turn your vision into a digital masterpiece that drives meaningful action and success.

Role Description

We're hiring our first dedicated Proposal Writer + Project Manager. This is a hybrid role by design: the person who scopes a project is the best person to deliver it. You'll own the engagement arc from "RFP hit our inbox" all the way through "site launched, client happy, final invoice paid."

This is not a junior role. You'll be working directly with the founder and the sales lead, with real ownership over what we bid on, how we respond, and how projects get delivered. If you've ever wanted to run your own agency but not deal with sales and ops, this role gives you 80% of that experience without the risk.

What You'll Own

Proposal side (approx. 50% of time):

• Triaging incoming RFPs and advising on bid/no-bid decisions based on fit, budget realism, and win probability
• Writing technical approach, methodology, past performance, executive summary, and pricing rationale sections
• Coordinating with the founder and sales lead on win themes, value ladder pricing, and strategic positioning
• Building and maintaining a reusable proposal library (case studies, boilerplate, technical capability matrices)
• Tracking win rates, loss reasons, and improving the playbook over time

Project Management side (approx. 50% of time):

• Running kickoff meetings for sold projects
• Managing scope, timeline, and budget across WordPress and Drupal redesign engagements
• Primary client communication --- status updates, escalation handling, stakeholder alignment
• Coordinating internal and external resources (designers, developers, QA)
• Sprint planning and execution in Asana, ClickUp, or Jira (we're flexible on tooling)
• Protecting project scope from creep and protecting the team from unrealistic client demands
• Post-launch wrap-up, retrospective, and handoff to support

What You Bring

Required:

• US citizenship (required for federal and higher-ed contract eligibility)
• Based in or able to work full PST business hours; Seattle metro preferred
• 5+ years combined experience in agency proposal writing and/or project management
• Proven track record of writing winning RFP responses for WordPress or Drupal redesign projects (samples required)
• Experience managing web redesign projects end-to-end --- kickoff to launch
• Strong working knowledge of WordPress and Drupal technical concepts (content modeling, accessibility, multisite, migrations, hosting platforms, editorial workflows)
• Familiarity with public sector, higher-ed, or enterprise RFP formats
• Excellent written and verbal communication
• Comfort with proposal tools (Proposify, PandaDoc, Qwilr, or advanced Google Docs) and PM tools (Asana, ClickUp, Jira)

Nice to have:

• APMP membership or certification
• Experience with Acquia or Pantheon hosting platforms
• Background writing federal RFP responses (SF-330, past performance narratives)
• Figma proficiency for reviewing design deliverables
• Experience with decoupled / headless CMS architectures

Compensation & Benefits

• Competitive base salary commensurate with experience (we'll discuss range in the first call based on your expectations)
• Performance bonus on proposal wins you personally authored
• Delivery bonus on projects you PM to on-time, in-scope completion
• Full remote work
• PTO and holiday schedule
• Health benefits
• Annual budget for professional development (APMP membership, conferences, certifications)

How to Apply

DM the founder directly on LinkedIn with:

1. Two redacted writing samples from real RFP responses you authored. Wins preferred; thoughtful losses also welcome (losses often teach more). Client names can be blacked out --- we care about your writing, not the logo.
2. A one-paragraph case study of a WordPress or Drupal redesign project you managed from kickoff to launch. Include timeline, team size, what went well, and what didn't.
3. Your salary expectations. A base range is fine; we'll discuss bonus structure in the first call.
4. Why DoodleWeb specifically. One or two sentences --- we read them.

No samples, no case study, no conversation. We don't run unpaid writing tests.

Our Interview Process

1. DM screening (reviewed within 72 hours)
2. 30-minute intro call with the founder
3. Paid trial: one real proposal, flat fee, 1-week turnaround
4. Final call with the founder and sales lead
5. Offer

• We aim to move from first DM to offer in under 3 weeks.